Simon Winter- Insuring The Past

What is an old yacht worth? Deciding such matters is Simon Winter’s bread and butter

- Rob Peake

Simon Winter tells a good story about hanging head first over the windward side of a fishing smack, banging along in a head sea, trying to squirt ‘gunk’ into a tiny seam in the hull that was threatening to sink the boat on the other tack. “We made it home, let’s put it that way,” he recalls with a laugh.

Tales of derring-do on working boats don’t quite fit with the stereotypical image of an insurance broker, but Winter was toddling around on smacks before he can remember and his family have owned working boats all his life – the smacks Rosa & Ada (1908), Unity of Lynn (1906 and on the National Register of Historic Vessels) and Maria (1886) and Bristol Channel pilot cutters Cornubia (1911) and Mascotte (1904 and also on the National Register of Historic Vessels).

His father left school to work on the Thames sailing barges in the last days of trading under sail, and ended up becoming chairman of Medway Ports. Winter Jnr went to the highly academic Canterbury school, before university and a stint in the City as an investment banker. He was running the yacht account for an insurance broker, thinking he’d found the best way of combining a passion with work (‘and to date I haven’t tired of it – that’s the danger!’), when family reasons persuaded him to move south west in 2006. He set up as Simon Winter Marine, specialising in classic boats (75% of his business is classic), and today insures most of the working boat fleet along with many classic yachts around the world, from 21ft canoe yawls to 100ft Fifes.